On Episode 661 of The New Media Show, host Rob Greenlee, 2017 Podcast Hall of Fame inductee, Chairperson of the Podcast Hall of Fame, and longtime new media executive, is joined by Dave Jackson, 2018 Podcast Hall of Fame inductee, founder of School of Podcasting, and Head of Podcasting at Podpage.com, for a deep conversation about whether independent podcasters and media creators can still win in today’s rapidly changing creator economy. This episode centers on a question many creators are quietly asking right now: Can indie podcasters still grow, monetize, and build trust in a market being reshaped by video, AI, platform control, and professionalized media production? Rob and Dave discuss the recent combination of Podpage and School of Podcasting, why podcast education matters more than ever, and how websites, email lists, communities, video, RSS, and AI-assisted workflows are becoming essential parts of a creator’s survival strategy. Dave joined Podpage as Head of Podcasting in 2024, and School of Podcasting has been helping creators launch, grow, and monetize podcasts since 2005.  The conversation also moves into some of the biggest issues facing podcasting and new media in 2026, including AI-generated shows, human voice and video cloning, creator burnout, YouTube’s influence on podcast identity, Apple’s HLS video podcast direction, and why human trust may become the most valuable asset creators have left. Rob and Dave bring decades of experience to this discussion. Both have seen podcasting shift through multiple technology waves, from the early RSS era to platform consolidation, video podcasting, AI tools, and the rise of creator-led media. That history makes this episode a practical and honest look at what indie creators need to do now to stay relevant, trusted, and discoverable. What does this episode cover? Can independent podcasters still succeed in a noisier, more competitive market? What does “winning” even mean now: downloads, money, trust, community, authority, or sustainability? Why the Podpage and School of Podcasting connection matters for podcast education and creator websites Why podcasters need a home base beyond social platforms and YouTube How AI is changing show notes, images, writing, research, production, and creator workflows Why AI-generated content should not all be treated as spam, but fraud and abuse must be addressed H